(2R,3S)-trans-3',4'-dimethoxyflavan-3-ol | 1196870-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R,3S)-trans-3',4'-dimethoxyflavan-3-ol
• CAS: 1196870-24-2
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: DQNVINLXRCCLFO-SUMWQHHRSA-N

反应信息

• 作为反应物：
  描述：

  (2R,3S)-trans-3',4'-dimethoxyflavan-3-ol 、 乙酸酐 在 吡啶 作用下， 以100%的产率得到(2R,3S)-trans-3-acetoxy-3',4'-dimethoxyflavan
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062
• 作为产物：
  描述：

  (1S,2S)-1-(3,4-dimethoxyphenyl)-3-[2-(methoxymethoxy)phenyl]propane-1,2-diol 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 (2S,3S)-cis-3',4'-dimethoxyflavan-3-ol 、 (2R,3S)-trans-3',4'-dimethoxyflavan-3-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of flavan-3-ol derivatives as positive modulators of GABAA receptors

  摘要：

  We herein describe the synthesis and positive modulatory activities of a small library of flavan-3-ol derivatives on alpha(1)beta(2)gamma(2L) GABA(A) receptors. Structure-activity relationships of various substituents on the A, B and C rings were evaluated in a functional electrophysiological assay. A trans configuration and a 3-acetoxy moiety are essential for activity. Substitution of the B ring appears to be well tolerated, with substituents on the A ring playing a major role in determining activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.062